We finally finished our D&D game of nearly seven years and statted up new ones for the next story - a swashbuckling adventure in the same world, ten years later. New characters mean new drawings, starting with the captain, Dami, and the quartermaster, Esh.  
Usually making characters for me is a solitary thing, but this time I brainstormed with another player and these characters fell in crazy, ridiculous, hundred-page-backstory love. To suit their romance novel backstory, I drew them in a romance novel scene - a concertina lesson belowdecks that is about one note away from being a lot more.​​​​​​​
Vector drawing in Adobe Illustrator.
Dami face detail. I play the captain, a lifelong sailor and longtime pirate. 
Esh face detail. He had to strongly resemble his father while still looking like his own person.
Concertina detail. I have a couple of cheap concertinas of my own that made decent references for the overall pose, but these two needed something much fancier. Thankfully there's an accordion/concertina-focused music store in western MA, so I was able to get lots of reference photos on a trip to Northampton.
Hand detail. Esh's left arm was an opportunity to inject a bit of his player into the drawing. Esh's arm hair is based off of reference photos of my friend's arms.
Ring detail. These two have rather ostentatious taste in jewelry, and it was fun to have the chance to draw so many rings.
The whole drawing in outline mode. Even on my 22" Cintiq, a lot of the most detailed areas are solid black.
Progress shots. I started this about a year ago and got stuck partway through. I went back to it after about 5 months of not even opening the file to take a peek, and I really think the time away did me a world of good. Sometimes it's helpful to get a bit of perspective.

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